Vacation rentals with a kayak in McHenry County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in McHenry County

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Guest favorite

A log-sided home is set against a clear blue sky, overlooking a heated pool. Lush greenery surrounds the pool area and a spacious deck features seating and umbrellas. The house showcases large windows and a balcony that opens to the serene landscape.

Villa in McHenry

4.93 out of 5 average rating, 40 reviews

Fabulous Cabin

WELCOME TO WATERFRONT LOG-SIDED HOME! ARTISAN CRAFTMANSHIP HOME OFFERS A BACKYARD OASIS SITUATED , NESTLED ON A PRIVATE POND, Heated POOL(closed till April 1st), Hot tub open from Oct 15th to Apr 15thGAZEBO, FIRE PIT, FISHING! 4 BEDROOMS AND 4.5 BATHS The homes sits on the highest point in the neighborhood and has stunning views in the front & backyard! Enjoy the mornings sitting on your front porch. The main floor is completed by an office, finished walkout basement in with a custom built bar

LocationValueQuiet

An open living area showcases large windows that provide views of the surrounding landscape. A dining table with four chairs is positioned near the kitchen, while a cozy seating arrangement features a sofa and flat-screen television. Natural wood accents create a warm environment.

Home in Richmond

4.88 out of 5 average rating, 176 reviews

"About Time" You will love it! -12 beds

We are SUPERHOSTS !!!- Look for all inclusive boat and wave runner packages through Twin Lakes Boat Rental. Swimming at the Sand Bar in the middle of the lake or at Lake Mary’s beach in Twin Lakes is best for kids. About Time has a spacious yard for corn hole/wiffleball, basketball, Kayaks & SUP's. There’s a large playfield is just 200 yards East too. Visit the Sand Bar Restaurant also, a must! The spring fed clear water is great for fishing & skiing. We love this place and know you will too.

LocationValueBathroom

Superhost

The exterior of a mid-century A-frame house showcases its striking triangular shape and steep slanted roof. Large glass doors provide a view of the interior, framed by an inviting deck area. Lush greenery surrounds the home, enhancing its connection with nature.

Cabin in Crystal Lake

4.91 out of 5 average rating, 23 reviews

The Fox Den / Midcentury A-frame

Our A-Frame is a mid-century gem with everything you envision in a cabin, plus all the comforts of home. It features a private dock with access to the Fox River and the Chain of Lakes, as well as direct entry to the Silver Creek Conservation Area. Located between the Fox River and the northern end of the Silver Creek Conservation Area, it’s only 1:15 from Chicago and 1:30 from Milwaukee. The ideal spot for a couple’s retreat, a small family adventure, or a solo escape to reconnect with nature.

Outdoor spacesLocationFamily

Guest favorite

The exterior of a two-story home is displayed, featuring a spacious deck above the entrance. A well-maintained lawn surrounds the property, accented by trees and shrubbery. The driveway leads to a two-car garage, and a pathway leads towards the entrance of the house.

Home in Algonquin

4.87 out of 5 average rating, 103 reviews

On the Fox River Front/Sauna/Hot Tub/Kayaks/Grills

On Fox River in Algonquin Kick back and relax in this calm, tastefully finished space. Nestled amidst a picturesque waterfront and greenery, this stylish property exudes an elegance, harmoniously blending into the serene natural surroundings. It is a perfect combination of comfort and convenience. Located within a short range to fantastic "Old Town District" of Algonquin/superb restaurants, pubs, entertainment as well as parks and trails, simply just mere moments away from array of amenities.

ValueOutdoor spacesTV

Guest favorite

A spacious outdoor patio features a wooden dining table surrounded by six matching chairs. Two colorful kayaks are mounted on the wall, while a private dock extends into the water, providing access for boating and fishing.

Home in McHenry

4.89 out of 5 average rating, 44 reviews

Waterfront House, 2 kayaks, Game room, Fire pit, B

Escape to this stunning waterfront house in McHenry, Illinois, offering a perfect blend of relaxation and adventure. Enjoy kayaking on the waterway leading to Pistakee Lake, fishing from the private dock, or simply unwind in the hammock. This home features a sunroom with water views, a game room for entertainment, and a cozy fireplace. With a fully equipped kitchen, outdoor seating, and a BBQ grill, it's ideal for families and groups seeking both outdoor activities and comfortable and relaxing

ValueOutdoor spacesBathroom

Guest favorite

A spacious back deck is highlighted, featuring an outdoor table with an umbrella and comfortable seating. A charcoal grill is positioned nearby, and vibrant flowers add a splash of color. The neighboring structures and lush greenery create a welcoming outdoor space.

Cottage in Fox River Grove

4.85 out of 5 average rating, 48 reviews

Waterfront Cottage/sauna/kayaks/firepit/dock

Enjoy some time away at this peaceful cottage on the Fox River. There is a dock with jet ski lift and kayaks available to guests. Large deck with ample seating. There is a sand beach with volleyball court and playground within walking distance of home. Many places to dine and shop nearby. Some nice resteraunts on the water. Local attractions nearby including Norge Ski Club, Bettendorf Castle, Three Oaks Rec, ect. Fire pit next to river with wood included. Amazing sunset view and steam sauna.

LocationValueBackyard

Guest favorite

A spacious living area is highlighted by large windows offering views of the water. Colorful seating options, including bean bags and patterned chairs, complement a wooden coffee table. Sleek ceiling fixtures and a soft rug define the gathering space, enhancing the open layout.

Home in Richmond

4.96 out of 5 average rating, 238 reviews

TheGlassCabin@HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

ValueLocationKitchen

Top guest favorite

Home in Wonder Lake

4.95 out of 5 average rating, 22 reviews

Comfort, just off the lake

Take it easy at this delightful and tranquil freshly rehabbed 2 bed 1 bath getaway. Need a long weekend, visit family, extended stay for work, or travel nursing commitment? Excellent hospitals nearby, a beach at the end of the block, seasonal boat, canoe, and paddle boards available to rent & local activities await you. Our home is very clean & quiet. Large (50% fenced) yard. Streets are lit with no sidewalks. Pre-approved pets are welcome. Additional shedding pet cleaning fee $50.

Outdoor spacesLocationComfort

Top guest favorite

Cottage in Wonder Lake

4.94 out of 5 average rating, 174 reviews

The Cozy Lake House, Dm me ?s Lake Front Property!

Welcome to The Cozy Lake House, your year-round haven for relaxation and celebration! Savor breathtaking sunsets, indulge in boating, watersports, and high-speed internet, and make special memories during holidays, bachelorette party's getaways, birthdays, family reunions, micro weddings, and more. With a fully equipped kitchen, spacious rooms, and the tranquil lakeside setting, every moment here is magical. Reserve your spot now and experience the ultimate in lakeside living!

LocationOutdoor spacesCheck-in

Superhost

An open-plan living and dining area is highlighted by a large dining table and comfortable seating arrangements. Natural light floods the space through expansive windows, with a fireplace adding warmth. Wooden beams adorn the ceiling, enhancing the inviting atmosphere.

Home in Wonder Lake

4.85 out of 5 average rating, 74 reviews

Luxury Lakefront Escape - 25 mins from Lake Geneva

Welcome to your dream vacation rental on Wonder Lake, IL and only 25 minutes from Lake Geneva! This stunning retreat is nestled right on the water, providing breathtaking views and a serene atmosphere. The rental boasts a beautifully designed interior, with spacious and comfortable rooms, modern amenities, and tasteful decor. With its prime location, you'll have direct access to the lake, where you can swim, fish, or simply relax on the private dock. BOAT RENTAL OPTION**

LocationValueFamily

Guest favorite

An expansive deck is illuminated by string lights, creating a warm ambiance in the evening. A dining set with red chairs is placed on the wooden flooring, with a fire pit nearby. The surrounding wooded area adds a natural backdrop to the outdoor space.

Home in McHenry

4.83 out of 5 average rating, 58 reviews

Private 1 Bed w/Loft on 5 Wooded Acres + Rock Wall

Relax & unwind in this distinctive & serene retreat. Nestled on more than 5 acres of wooded land that extends to a secluded nature preserve, this accommodation promises a peaceful & private escape. Recently renovated, the space offers a memorable experience with extensive trails, foot bridges over creeks, and a secluded pond. For a unique sleeping experience, ascend the rock wall to reach the lofted queen bed, or opt for the ladder if you prefer an easier ascent.

Outdoor spacesLocationLong stay

Guest favorite

A wooden deck is visible, featuring a glass-top dining table surrounded by metal chairs. The tranquil lake stretches out beyond, with clear blue skies and calm waters. A tree's branches provide shade, enhancing the outdoor seating area by the water.

Cottage in McHenry

4.88 out of 5 average rating, 57 reviews

Lakefront Views, Free Water Sports!!

Relax at this stunning lake house on Lake Pistakee. Enjoy this cozy house with a private lakefront view on a sleepy dead end street. This lake house underwent a full rehab in 2019. House features its own private dock right on the water and includes 2 free kayaks, 2 free paddle boards, and a free paddle boat to use. Enjoy the fire pit overlooking the water and free gas grill (byow). Lake Pistakee is on the Chain o Lakes which includes 14 connected lakes

LocationOutdoor spacesIndoor spaces